Known as the Steel City, Pittsburgh forged its identity under a banner of hard work, industry and hardline blue-collar ethos. Jobs were plentiful during most of the 19th and 20th centuries, attracting iron-willed immigrants from across the globe. Despite the influx of fresh faces, industry took its toll on the city, staining many of the city’s buildings and attracting bad press the world over. By the 1950s, Pittsburgh had committed itself to cleaning up, and invested resources into a city-wide beautification project. The steel mills and shipping yards that built Pittsburgh into an international household name were preserved, even sanctified, while revamped urban infrastructure left room for ideas and communities to grow up together. Soon, Pittsburgh’s universities pulled the town into the spotlight once again, his time as a recreation destination and hotbed of higher learning and fresh business ventures.

Album: The Doors – The Soft Parade
Book: The Perks of Being a Wallflower – Stephen Chbosky
Movie: The Mysteries of Pittsburgh (2008)
Season: Anytime

The Strip District

Like many great American cities, Pittsburgh is a city of immigrants. Dozens of cultures, cuisines, and customs come together in the city’s historic Strip District, a neighborhood once known as the city’s shipping and receiving area for goods bound for trips up or down either of the city’s three rivers. Old world spice markets, butcher shops, delis, cheese counters, fishmongers and flower stalls add color to the Strip’s brick and steel industrial hues. Pennsylvania Macaroni Co. will give you plenty of options for home cooking, as will Stamoolis Brothers next door.

Wood Street Galleries

601 Wood St

The Wood Street Galleries are probably The ‘Burgh’s best-kept secret, which is a shame, because they’re not just fun, but incredibly impressive, as well. Tucked up above Wood Street station, these galleries are funded by the Heinz Foundation and showcase quarterly interactive, immersive exhibitions by artists from all over the world. Never crowded, the intimacy of the galleries can almost prompt an eerie sensation as you submit mind and body to the will of the faceless artist. The small, out of date steel elevator is the perfect (and only) way to reach the galleries, so don’t bother looking for an alternative entrance or exit.

Cathedral of Learning

4200 Fifth Ave

The view from the 42nd floor is unlike any other in the city. Seriously– It’s the tallest educational building in the western hemisphere and the second-tallest university building in the world. “Cathy,” as the building is affectionately known by Pitt students, is definitely worth a visit. Twenty-nine Nationality Rooms (designed by representatives of the countries they’re modeled after) adorn the first floor. Be sure to peak into each during the holidays, when the rooms are decorated according to their countries’ holiday traditions. With Schenley Park and Panther Hollow a short walk away, there’s plenty to explore within walking distance of Cathy.

View From Mt. Washington

The humble summit of Mt. Washington isn’t famous for its daunting elevation or change in climate. Instead, it’s 367 feet has made it the best vantage point in all of Pittsburgh. With a view of the entire city, it’s hard not to fall in love with the town while you’re up there. Named after George Washington. the mountain is where the young colonist set up shop in 1770, when he was tasked with surveying the land below for the English Crown. Two funiculars survive from the area’s days as “Coal Hill,” when dozens of inclines shuttled workers and materials up and down the mountain.

See a Game at PNC Park

115 Federal St

You don’t have to be a baseball fan to appreciate nine innings of this view. The ‘great American pastime’ has never looked so good, as the recently resuscitated Pittsburgh Pirates play in one of the most stunningly beautiful ballparks in the country. Located across the Allegheny River from downtown, PNC Park is set in Pittsburgh’s North Shore neighborhood, a district connected to downtown by the Clemente, Warhol and Carson bridges. The city’s skyline remain’s visible from just behind the outfield, giving twilight and night games a decidedly magical feel. Tickets are usually easy to come by, too.

Jerry’s Record’s

2136 Murray Ave

Jerry has more vinyl on his shelves than an IKEA factory, and we’re convinced you can find just about anything here. The tall shelves make it feel like you’re wandering through a cavern of LPs, and the crates of 45s in the back would have every underground DJ in Berlin drooling. We joke that there’s a twenty dollar cover at Jerry’s, because you can’t possibly make it out without finding twenty dollars worth of music you never realized you needed so desperately. The prices are far more reasonable than anywhere else we’ve been, and the Squirrel Hill neighborhood is a great detour through the Steel City.

Caliban Books

410 S Craig St

Where else can you find first editions of children’s books alongside rare works by Gary Snyder and Jack Kerouac, alongside extensive writings on the history of Western Pennsylvania, all at the same address? The staff is helpful, and one rarely knows what to expect in this independent bookstore. Caliban is also home to Desolation Row Records– It’s a small collection of newly released and used vinyl, but it is incredibly well-curated. Never a bad find here. Bonus points if you explore the nearby shops on South Craig St!

Andy Warhol Museum

117 Sandusky St

Yes, Andy Warhol was born, raised, and buried in Pittsburgh, Pennsylvania. The Warhol has developed into modern and pop art’s premier landing pad, hosting countless seminars, exhibitions, films, and performances. Perhaps most importantly though, is the museum’s vast collection of Warhol’s work. Multiple floors display over 900 original paintings, and more than 4,000 of Warhol’s film or video projects. You could easily spend several completely mesmerized hours here on Sandusky Street.

Primanti Bros.

46 18th St

What’s become somewhat of a national sensation began right in the Strip District. Massive sandwiches, obscenely overstuffed with coleslaw and french fries, are the core of Primanti Bros’ menu. Pick your meat, your beer, sit down and take what comes. It’s very simple…until you realize you have an entire second half of your sandwich left to finish. With several locations around the city (the newer chain restaurants are not at all the same experience), 18th St was, and always will remain, the original Primanti’s. Local heroes like Fred Rogers, Dan Marino, and Mario Lemieux are painted on the walls, and, we must say, all make great lunch dates.

East End Food Co-Op

7516 Meade St

The year is 1980: the steel industry has collapsed, the Cold War rages on, and the East End Food Co-Op opens its doors. Before juice bars and hip farmer’s markets were a staple in most ‘Burgh neighborhoods, East End was providing fresh and locally-sourced groceries to an area of the city that’s still kind of gritty today. The place’s authentic back alley feel (the front door of the Co-Op is literally in a shady-looking alley), and the vegetarian café makes East End a must-visit. It’s also within walking distance of Frick Park, making it optimal for picnicking or post-grocery wandering.

Kayak Three Rivers At Once

33 Terminal Way #537

We just think it’s really cool that you can paddle your way out into where the Monongahela, Allegheny and Ohio Rivers converge peacefully. If you’re up for it, an early fall afternoon might be a perfect time, when Steelers fans tailgate, not just on the riverbanks, but actually on the rivers, too, in their boats. You’re likely to be tossed cans of domestic beer, maybe even handed a plate of pierogies and kielbasa. For the record, several of us here at Ancora have fallen out of our kayaks more than once and were pleasantly surprised by the cleanliness of the Steel City’s rivers. If kayaking isn’t your thing, try stand-up paddle boarding. Companies around town even offer paddleboard yoga classes!

Dive Bars

Dive Bars: Three of the greatest dive bars known to humankind are right here in the heart of ‘Yinzer’ nation. First, the Bloomfield Bridge Tavern (4412 Liberty Ave), where you can partake in the hands-down best pierogies in the city and perhaps talk nice bartenders into free shots of Polish blackberry brandy. Next, Belvedere’s (4016 Butler St), a hole-in-the-wall that serves fantastic tacos for $5 and Iron City tallboys for $1.50. Thursday is 80s night, too – absolutely worth a trip. Finally, Gooski’s (3117 Brereton St), in the heart of Polish hill, is a one-of-a-kind experience: imagine a hip, gritty, big city bar with numerous craft beer selections– Add pool/ping pong tables, a pinball machine, and finally your grandmother’s kielbasa and haluski. All three locations are also concert venues.

Construction Junction

214 N Lexington St

Salvageable leftover scraps from building projects across the city (and probably all of Alleghany County) are collected here and then resold for use as recycled elements of newer construction or art projects. The fleet of colorful porcelain toilets might make you giggle, but a walk around this old warehouse will more than likely have you mentally redesigning your own domestic space. One of the bonuses to this trip is the pleasant drive or bike ride through the University of Pittsburgh campus in the Oakland neighborhood and, if you’re clever, the sprawling Schenley Park, which houses part of Carnegie Mellon’s campus.

Oh Yeah! Ice Cream & Coffee

232 S Highland Ave

Set back from Bakery Square and the recently gentrified mash-up that is East Liberty-Shadyside-Friendship sits Oh Yeah! It really is an anomaly – part digital startup (we think), part coffee roastery, part ice cream/waffle house. It’s probably the only place in town where one can order a vegan waffle with dairy-free ice cream, topped with goat cheese, balsamic vinegar, and cookie batter. A projector mounted on the wall shows daily features (Monday is Merrie Melodies night), and a record/book library take up most of the wall space. Donate a book without taking one and you’ll get a free cup of coffee! Suggested: The Big Lebowski – White Russian-flavored ice cream (Parts of the film were shot in nearby Trafford).


Portland, Williamsburg, The Mission, and Lawrenceville. The city’s biggest neighborhood is also its hippest. Take a stroll down Butler Street for boutique stores, classic salons, coffee shops, and nearly every type of restaurant imaginable, from funky Mexican to high-end Italian to college sports bar. Bowl in Arsenal Lanes, catch a craft beer and movie at Row House Cinema, or get some fresh air at Arsenal Park. Suggestions: Round Corner Cantina (their margaritas are fantastic), Church Brew Works (it’s a brewery inside of an old church!!!), the Pittsburgh Juice Company, and Wild Card, a funky card store. Because cards can be funky.

Bicycle Cafe

2518 E Carson St

Our favorite burgers in Pittsburgh. We could stop there, but figure we should bring up their impressive beer selection and engagement with the local bicycling community. Many of Pittsburgh’s favorite local beers are available on tap and are competitively priced (Carson Street is no place for shiesty bar owners, their business wouldn’t survive). Bicycle Cafe sponsors several road races throughout the year, and it seems like many of its patrons are excited to talk about various mountain biking trails in the area, even those an hour or so down the road in West Virginia. A satisfying stop on several fronts.

Sampsonia Way

Located in Pittsburgh’s historic North Side (just a few blocks from PNC Park) are the Mexican War Streets, a neighborhood known for it’s beautiful, late-nineteenth century architecture and quirky decor. The quirkiest street in the neighborhood (maybe even the city?), though, has to be Sampsonia Way. It’s home to Randyland (1502 Arch St), part-time art project, part-time social experiment, and full-time home to Randy Gilson and City of Asylum (330 Sampsonia Way), a housing and art project (which sometimes doubles as a public venue) given to writers who are exiled from their home countries.

Beehive Coffee

1327 East Carson Street

It isn’t hard to find to a cup of coffee on the South Side of town, but The Beehive makes a great pit stop if you’ve ventured down to Carson Street for a concert or show. The wifi is as strong as the dark roast, and the only way you’ll ever feel rushed out of the place is if the barista gets a little carried away with the stereo volume. Might sound funny, but check out the bathrooms in this place before you leave– They’re wild.